I am looking into upgrading our company computers to a newer OS as we are mostly running XP for users with a balance of 2003/2008/2012 for the servers. AD is on 2003 and Outlook, the same. Our environment is now mostly web based apps and the most of the applications which aren't will migrate over to web apps within the next year.

I am sure you can imagine some of the issues we have in this day and time with that setup so we are in need of modernising!

We don't anticipate upgrading for another six months so when we do, Win 10 should be stable enough option plus 2016 for the server (hopefully).

So the question is, do we upgrade all desktops to Windows 10 and servers to 2016 or do we just get a couple of Terminal Servers with CALs to cover? Which would be the better option and which is the cheaper?

While I don't have an immediate answer for you, there were several things that came to mind in your above post.

1) What is your current AD function level? 2003 to 2016 is a huge jump. You may have to do a rolling upgrade in AD function level from 2003 to 2016, or will you just start a new AD with 2016?

2) With the majority of your current desktop hardware fleet on XP, are you sure your desktops hardware will support Win10 requirements? You may be better off just replacing the hardware with OEM Win10 boxes.

3) If you switch over to RDS what device will you put on the desktop as a user interface. That also needs to be factored into the cost of the solution. I think you will find it will be pretty close in cost between the two solutions. You also need to be aware and confirm that all of your software is RDS friendly.

4) If all of your applications are going to be web based, would chrome based netbooks be a desktop solution if you implement an RDS server?

5) You also have to consider the collateral costs of moving from XP to Win10 in that what other software must be upgraded that will not run on Win10, since I assume you will move from XP x86 to Win10 x64. (thinking peripheral and hardware drivers)

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While I don't have an immediate answer for you, there were several things that came to mind in your above post.

1) What is your current AD function level? 2003 to 2016 is a huge jump. You may have to do a rolling upgrade in AD function level from 2003 to 2016, or will you just start a new AD with 2016?

2) With the majority of your current desktop hardware fleet on XP, are you sure your desktops hardware will support Win10 requirements? You may be better off just replacing the hardware with OEM Win10 boxes.

3) If you switch over to RDS what device will you put on the desktop as a user interface. That also needs to be factored into the cost of the solution. I think you will find it will be pretty close in cost between the two solutions. You also need to be aware and confirm that all of your software is RDS friendly.

4) If all of your applications are going to be web based, would chrome based netbooks be a desktop solution if you implement an RDS server?

5) You also have to consider the collateral costs of moving from XP to Win10 in that what other software must be upgraded that will not run on Win10, since I assume you will move from XP x86 to Win10 x64. (thinking peripheral and hardware drivers)

At this point I wouldn't really put my focus on the desktops, if how they will operate in the not too distant future is changing, then the devices you buy maybe too.

I would focus on trying to get your server OSes on a similar platform - forget 2016 if your waiting 6 months for Win10 to stabilize.

Get your 2003 machines removed if they have no valid reason still existing, get the domain and forest level looked at - I wouldn't even want to consider putting Win10 or Server 2016 in the mix with 2003 and XP, I would want all of these as ready to go as possible first.

If by outlook you meant exchange - I would look at getting that up to a supported platform too, if any of your EOL systems fail, you have no support, this would be my biggest concern.

You could promote the 2012 server (depending on what it's duties are now) to the primary DC and then demote the 2003 server, this way you are getting that EOL server out of the mix and taking a step toward 2016 server when ever it becomes available. Is the 2003 server a small business server as it kind of sounds like it with you saying AD and Outlook (I assume you meant Exchange) is on the same version OS. If that is the case then you would want to add a new Exchange server and migrate to the newest version of Exchange (as well as purchase Exchange CALs and AD User CALs for 2012) as you wouldn't want to run Exchange and primary DC on the same server.

As for the desktops really it is up to you on what you want to do. I would say either way you really need to get away from XP as it is past EOL and is not getting any security updates which means you network is open to vulnerabilities in the wild. I would probably say replacing all XP PC with new hardware is best option and in 6 months it should be standard on all hardware coming from vendors.

You also said that you recently purchased hardware that you wanted to upgrade? Did you buy new hardware and install Windows XP on them? How long ago was that hardware purchased as installing XP on new hardware seems kind of backwards to me so just trying to understand the whole new hardware thing.

So, finally, do we get cheap OEM 7/8.1 Pro licences for each of the machines then upgrade each to 10 (within the year) or move straight onto a Volume Licence..

A couple of additional questions then.

I'm assuming that since you have XP on these machines the hardware is several years old, unless you are installing XP on fresh hardware.

That fresh hardware should have Vista or newer OEM license on it. If that is the case with a huge amount of effort you can use the free upgrade to Win10 as long as you do this in the first year that MS is offering this program. If you have more than 20 systems I would just go the VLK route and avoid the upgrade/wipe/reload fresh route.

Understand that OEM license live and die with the hardware. I'm not sure what you mean about getting cheap OEM 7/8 pro licenses. This would imply that you are also getting cheap new hardware? (I really know what you mean, but what you suggest is against the EULA).

How many systems are in your fleet of workstations (desktops and laptops)? That may give a better indication of the path you should take.

Unfortunately we have been installing XP onto newer hardware although we have hit issues here with some machines not having device drivers for XP. We had a large number of XP licences hence the reason for this. Some of the newer machines do have OEM licences on them but most are Home Editions and therefore useless to us.

For buying OEM licences, I was under the impression I could buy something as simple as a CD drive for the OEM licence to apply on an existing computer. I could be completely wrong with this these days though.

The total count should be around 50, so I'm sure from the information in this thread, VLK is the way to go.

For buying OEM licences, I was under the impression I could buy something as simple as a CD drive for the OEM licence to apply on an existing computer. I could be completely wrong with this these days though.

The total count should be around 50, so I'm sure from the information in this thread, VLK is the way to go.

The OEM license is tied to the motherboard and not any device.

The VLK route will be your best bet then since it is an upgrade to any existing OEM licensed system. The VLK then would allow you to retain your initial investment as you age out older systems. Where the externally purchased OEM licenses would die with the aged out system.

While this is a topic for another thread: I would consider for you to setup a Microsoft MDT server (free to setup) to build a reference image for your to deploy to those 50 workstations since you will be going the VLK route (I suggest hosting the KMS server on your site). This way all workstations are starting out with the same build. You can preload certain software into your reference image to save you time during deployment. Once your reference image is built then you sysprep and capture it. Then you will be able to deploy it to your hardware fleet, right from within MDT. If you have time, now is the best time to work on this MDT server and your reference image. If you had much more than 50 I might recommend you use WDS or FOG to deploy your reference image.

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